Dichloromethane → (1-(4-Oxopentyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Hydriodic Acid Salt

HRID 323346

Reaction equation

HRID 323346 reaction equation
[O:1]=[C:2]([CH3:29])[CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1.ClCCl.[IH:33]>O>[IH:33].[O:1]=[C:2]([CH3:29])[CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24841Hydrogen iodideHCID 22009233(1-(4-oxopentyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

Product 1

HCID 86756597(1-(4-Oxopentyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Hydriodic Acid Salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine (1-(4-oxopentyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine, ethylene ketal (0.9 g, 2.0 mmol) and dichloromethane (20 mL). Cool in an ice bath and add hydriodic acid (0.53 mL, 57%, 4.05 mmol). Warm to ambient temperature. After 0.5 hours, add water (0.5 mL) and heat to reflux. After 18 hours, cool to ambient temperature and evaporate in vacuo to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. temperatureheat to reflux
  3. waitAfter 18 hours
  4. temperaturecool to ambient temperature
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-70c33d0dc40746d3859726d21fe62f3e
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

Loading…